CN105601506A - 2,5-dibromo-1,4-biphenoxyl cobaltous diacetate complex single crystals and application - Google Patents

2,5-dibromo-1,4-biphenoxyl cobaltous diacetate complex single crystals and application Download PDF

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CN105601506A
CN105601506A CN201610001152.2A CN201610001152A CN105601506A CN 105601506 A CN105601506 A CN 105601506A CN 201610001152 A CN201610001152 A CN 201610001152A CN 105601506 A CN105601506 A CN 105601506A
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nitrae
isosorbide
bis
benzene
bromo
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王英
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Tianjin University
Tianjin Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/418—Preparation of metal complexes containing carboxylic acid moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
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    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract

The invention discloses 2,5-dibromo-1,4-biphenoxyl cobaltous diacetate complex single crystals and application. The structure of the 2,5-dibromo-1,4-biphenoxyl cobaltous diacetate complex single crystals is Co2+.[L2-], wherein L is 2,5-dibromo-1,4-biphenoxyl oxalic acid. Meanwhile, the invention discloses a preparation method of the single crystals. A normal-temperature volatilization method is adopted, that is, L and Co(NO3)2.6H2O are stirred in water for half an hour and then filtered, and filtrate volatilize for two weeks at normal temperature to obtain the pink blocky crystals suitable for X-ray single crystal diffraction. The molar ratio of L:Co(NO3)2.6H2O is 1:1. The application of the 2,5-dibromo-1,4-biphenoxyl cobaltous diacetate complex single crystals in detecting the adsorption amount of dyes or an illuminating agent as a potential fluorescent material is further disclosed.

Description

Bromo-Isosorbide-5-Nitrae-the benzene of 2,5-bis-dioxy base cobaltous acetate complex monocrystal and application
The present invention obtains state natural sciences fund general project (21471113), Tianjin Education Commission general project(20140506) and the academic innovation of the young and middle-aged teacher of Tianjin Normal University advance the subsidy of planning item (52XC1401).
Technical field
The invention belongs to organic and inorganic synthesis technical field, relate to the bromo-Isosorbide-5-Nitrae-benzene of 2,5-bis-dioxy base cobaltous acetate and joinCompound monocrystalline Co2+·[L2-] preparation method and as the application of potential fluorescent material, wherein, L=2, the bromo-Isosorbide-5-Nitrae of 5-bis--Benzene dioxy base oxalic acid.
Background technology
1,2,4-triazole and derivative thereof have the coordination feature of pyrazoles and imidazoles concurrently, are that the bridging that coordination ability is stronger is joinedBody, has synthesized at present and has characterized a large amount of monokaryons, multinuclear and multidimensional compound. These parts can be former with the nitrogen on 1,2Son forms N1 with metallic ion coordination, N2-bridging pattern, for 4 unsubstituted 1,2,4-triazole derivative can pass through 2,4On nitrogen-atoms form N2, N4-bridging pattern, this N2, N4-bridging pattern is with the N1 of imidazoles in metalloenzyme, N3-bridging patternSimilar. Also show in the design of molecular device for the specific use of triazole class compounds, synthetic have different dimensionsMetal complex has been the vital step of device.
The present invention adopts normal temperature volatility process, i.e. L and Co (NO3)2·6H2O filters stir half an hour in water after, filterLiquid normal temperature obtains applicable X-ray single crystal diffraction pink colour bulk crystal structure after volatilizing two weeks is Co2+·[L2-], wherein, L=Bromo-Isosorbide-5-Nitrae-the benzene of 2,5-bis-dioxy base oxalic acid. This complex also can be used as potential fluorescent material aspect and is applied.
Summary of the invention
The inventor provides following technical scheme for this reason:
The monocrystalline of the bromo-Isosorbide-5-Nitrae-benzene of a kind of 2,5-bis-dioxy base cobaltous acetate complex, is characterized in that this mono-crystalline structures adoptsAPEXIICCD single crystal diffractometer, uses the Mok alpha ray through graphite monochromatization, and λ=0.71073 is incident radiation, withω-2 θ scan mode is collected point diffraction, obtains cell parameter, from difference Fourier electron-density map through least square refinementUtilize software to solve monocrystalline data:
Its structure is as follows:
Co2+·[L2-], wherein
L=2, the bromo-Isosorbide-5-Nitrae-benzene of 5-bis-dioxy base oxalic acid.
The present invention further discloses the preparation method of the bromo-Isosorbide-5-Nitrae-benzene of 2,5-bis-dioxy base cobaltous acetate complex monocrystal,It is characterized in that it is to adopt normal temperature volatility process, by L and Co (NO3)2·6H2O filters stir half an hour in water after, and filtrate is normalTemperature volatilization obtains being applicable to the pink colour bulk crystals of X-ray single crystal diffraction after two weeks; Wherein L:Co (NO3)2·6H2The mol ratio of OFor 1:1;
The structure of the bromo-Isosorbide-5-Nitrae-benzene of 2,5-bis-dioxy base cobaltous acetate complex monocrystal is Co2+·[L2-]; Wherein L=2,5-bis-is bromo-Isosorbide-5-Nitrae-benzene dioxy base oxalic acid;
L。
The present invention further discloses the bromo-Isosorbide-5-Nitrae-benzene of 2,5-bis-dioxy base cobaltous acetate complex monocrystal as potential glimmeringThe application of luminescent material aspect the adsorbance of detection dyestuff or luminous agent, experimental result shows:
(1) complex monocrystal in embodiment 2 has well selective and sensitivity to dyestuff, and detectability reaches 0.1ppm。
(2) can detect the luminous agent of trace, detection limit reaches 5.0 μ g/L.
(3) complex monocrystal that prepared by embodiment 2 is 1.4 × 10 for the adsorbance of dyestuff-3mol/cm2。
Preferred example of the present invention:
The preparation of the bromo-Isosorbide-5-Nitrae-benzene of 2,5-bis-dioxy base oxalic acid (L)
2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol: chloroacetic mol ratio is 1:4
In tri-mouthfuls of round-bottomed flasks of 50mL that magneton, reflux condenser and thermometer are housed, add respectively 2,5-dibromobenzene-Isosorbide-5-Nitrae-Glycol (1mmol) and monoxone (4mmol), start and be stirred in 150oC, reacts 24 hours. After reaction finishes, by reactant liquorBe down to room temperature, the precipitation obtaining is added to 100mL hot methanol, after stirring and dissolving, filter, filtrate slowly volatilization obtains white admittedlyBody, yield 85%. Elementary analysis (C10O6H8Br2) theoretical value (%): C, 31.28; H, 2.10. Measured value: C, 31.24; H, 2.15;
2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol monoxone.
The present invention preferably 2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol: chloroacetic mol ratio is 1:4,150 DEG C of reaction temperatures, reaction24 hours time. Adopt " one kettle way ", 2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol and monoxone are prepared to 2,5-bis-under heating conditionBromo-Isosorbide-5-Nitrae-benzene dioxy base oxalic acid (L).
Another preferred embodiment of the present invention
Bromo-Isosorbide-5-Nitrae-the benzene of 2,5-bis-dioxy base oxalic acid (L) (0.1mmol) and Co (NO3)2·6H2O (0.1mmol) is at water(10mL) after stirring half an hour in, filter, filtrate normal temperature obtains being applicable to the pink colour bulk of X-ray single crystal diffraction after volatilizing two weeksCrystal. Productive rate: 40%. Elementary analysis (C10H6Br2CoO6) theoretical value (%): C, 27.24; H, 1.37. Measured value: C, 27.33; H,1.35。
Disclosed by the invention a kind of 2, the advantage that the bromo-Isosorbide-5-Nitrae-benzene of 5-bis-dioxy base cobaltous acetate complex monocrystal has andFeature is:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) the present invention prepared 2, the bromo-Isosorbide-5-Nitrae-benzene of 5-bis-dioxy base cobaltous acetate complex monocrystal, production cost is low,Method is easy, is applicable to large-scale production. Can solve at dyestuff or luminous agent application aspect the photoelectric respone scope of widening dyestuffProblem.
Brief description of the drawings
Fig. 1: the crystal structure figure of complex monocrystal;
Fig. 2: the two-dimensional layered structure figure of complex monocrystal.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described further, and embodiment is only indicative, never means itLimit the scope of the invention by any way. Raw materials used as 2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol, monoxone etc. all have commercially available, do not haveHave through continuing to purify but directly use.
Embodiment 1
2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol: chloroacetic mol ratio is 1:4
In tri-mouthfuls of round-bottomed flasks of 50mL that magneton, reflux condenser and thermometer are housed, add respectively 2,5-dibromobenzene-Isosorbide-5-Nitrae-Glycol (1mmol) and monoxone (4mmol), start and be stirred in 150oC, reacts 24 hours. After reaction finishes, by reactant liquorBe down to room temperature, the precipitation obtaining is added to 100mL hot methanol, after stirring and dissolving, filter, filtrate slowly volatilization obtains white admittedlyBody, yield 85%. Elementary analysis (C10O6H8Br2) theoretical value (%): C, 31.28; H, 2.10. Measured value: C, 31.24; H, 2.15;
2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol monoxone.
The present invention preferably 2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol: chloroacetic mol ratio is 1:4,150 DEG C of reaction temperatures, reaction24 hours time. Adopt " one kettle way ", 2,5-dibromobenzene-Isosorbide-5-Nitrae-glycol and monoxone are prepared to 2,5-bis-under heating conditionBromo-Isosorbide-5-Nitrae-benzene dioxy base oxalic acid (L).
Embodiment 2
Bromo-Isosorbide-5-Nitrae-the benzene of 2,5-bis-dioxy base oxalic acid (L) (0.1mmol) and Co (NO3)2·6H2O (0.1mmol) is at water(10mL) after stirring half an hour in, filter, filtrate normal temperature obtains being applicable to the pink colour bulk of X-ray single crystal diffraction after volatilizing two weeksCrystal. Productive rate: 40%. Elementary analysis (C10H6Br2CoO6) theoretical value (%): C, 27.24; H, 1.37. Measured value: C, 27.33; H,1.35。
Embodiment 3
Crystal structure determination adopts APEXIICCD single crystal diffractometer, uses the Mok alpha ray through graphite monochromatization, λ=0.71073 is incident radiation, collects point diffraction with ω-2 θ scan mode, obtains cell parameter through least square refinement,Utilize software to solve crystal structure from difference Fourier electron-density map, and through Lorentz lorentz and polarity effect correction. All H are formerSon is synthesized by difference Fourier and determines through desirable position calculation. Detailed axonometry data:
Embodiment 4
The concrete instance that dyestuff or luminous agent use
Method: differentiated pulse volt-ampere (DPV) the curve negotiating Princeton Applied Research Laboratory development of dye solutionPARSTAT2273 electrochemical workstation is measured. The DPV test of solution adopts three-electrode system, and glass-carbon electrode is working electrode,Auxiliary electrode is platinum plate electrode, homemade Ag/AgNO3Electrode is reference electrode; Electrolyte is the acetonitrile of 0.1molL-1TBAPSolution. Reversible to as interior mark taking Oxidation of Ferrocene reduction, obtain the corrected value between test system and standard hydrogen electrode system.
Monochromatic incident light photoelectric transformation efficiency (IPCE) is described the photoelectric transformation efficiency of DSCs under monochromatic light effect, is to turnMove on to the electron number of external circuit and the ratio of incident light subnumber. When measurement, use 500W xenon lamp as light source, incident light processThe multifunctional assembled grating spectrograph of WDS-5 type obtains the monochromatic light under different wave length λ; Monochromatic light irradiates the light sun in batteryThe utmost point, by Keithley2400 digital sourcemeter reading current value I. Monochromatic good fortune illumination is micro-by USB4000plug-and-playType light spectrometer measurement.
Step: understand dyestuff at TiO for definite2Adsorbance on film, complex monocrystal dyestuff prepared by embodiment 2Sensitization TiO2(geometric area is about 1cm to nanometer crystal film2) be immersed in 10mL0.01molL-1The methyl alcohol of NaOH moltenIn liquid, spend the night, treat that dyestuff separates the absorbance of attached mensuration solution completely. Wash one's face and rinse one's mouth and can calculate according to absorbance and molar absorptivityThe adsorbance of dyestuff on unit are nanometer crystal film. The adsorbance of this complex monocrystal is 1.4 × 10-3mol/cm2。
Result: compared with the methanol solution of dyestuff, complex monocrystal dyestuff is at TiO2Absorption spectrum on film all obviously becomesWide and red shift. This shows that dye molecule is at TiO2Form the J-aggregation of first and tail. From the operation principle of DSCs, dyestuff is poly-Spectrum broadening and red shift that collection causes are very favourable for the widening of photoelectric respone scope of dyestuff. But meanwhile, dyeMaterial aggregation can reduce its electron injection efficiency greatly, thereby causes the performance of DSCs low. So, conventionally in dye solutionAdd coadsorbent to suppress the gathering of dyestuff. This complex monocrystal is in methanol solution and at TiO2Purple on membrane electrode is moltenThe fluorometric investigation of liquid adopts 2.5 × 10-5The methanol solution of mol/L, maximum emission wavelength is positioned at 500nm.
Embodiment 5
Bromo-Isosorbide-5-Nitrae-the benzene of 2,5-bis-dioxy base cobaltous acetate complex monocrystal is as the application of preparing luminescent material.
Method: by sepectrophotofluorometer, carry out respectively excitation wavelength and the transmitting of this compound monocrystal (embodiment 2)The scanning of wavelength, selects and definite optimal wavelength.
Conclusion: the excitation wavelength of this compound and emission wavelength are respectively 340nm and 500nm.
Step: by bromo-2,5-bis-Isosorbide-5-Nitrae-benzene dioxy base cobaltous acetate complex monocrystal grind compressing tablet become external diameter be 27mm,The sheet sample of the about 3mm of thickness, puts into the sample cell of MPF-4 XRF and measures.
Result: the excitation wavelength lambda of this compoundex=340nm, emission wavelength lambdaem=500nm。
Describe in detail preferred embodiment after, being familiar with this technology personage can be well understood to, do not depart from above-mentionedUnder claim and spirit, can carry out various variations and amendment, all foundations technical spirit of the present invention is to above embodiment instituteAny simple modification, equivalent variations and the modification done, all belong to the scope of technical solution of the present invention. And the present invention is not also illustratedThe restriction of example embodiment in book.

Claims (3)

1. one kind 2, the monocrystalline of the bromo-Isosorbide-5-Nitrae-benzene of 5-bis-dioxy base cobaltous acetate complex, is characterized in that this mono-crystalline structures adoptsAPEXIICCD single crystal diffractometer, uses the Mok alpha ray through graphite monochromatization, and λ=0.71073 is incident radiation, withω-2 θ scan mode is collected point diffraction, obtains cell parameter, from difference Fourier electron-density map through least square refinementUtilize software to solve monocrystalline data:
Its structure is as follows:
Co2+·[L2-], wherein
L=2, the bromo-Isosorbide-5-Nitrae-benzene of 5-bis-dioxy base oxalic acid.
2. described in claim 12, the preparation method of the bromo-Isosorbide-5-Nitrae-benzene of 5-bis-dioxy base cobaltous acetate complex monocrystal, its feature existsTo adopt normal temperature volatility process in it, by L and Co (NO3)2·6H2O filters stir half an hour in water after, filtrate normal temperature volatilization twoAfter week, obtain being applicable to the pink colour bulk crystals of X-ray single crystal diffraction; Wherein L:Co (NO3)2·6H2The mol ratio of O is 1:1;
The structure of the bromo-Isosorbide-5-Nitrae-benzene of 2,5-bis-dioxy base cobaltous acetate complex monocrystal is Co2+·[L2-]; Wherein L=2,5-bis-Bromo-Isosorbide-5-Nitrae-benzene dioxy base oxalic acid;
L。
3. described in claim 12, the bromo-Isosorbide-5-Nitrae-benzene of 5-bis-dioxy base cobaltous acetate complex monocrystal exists as potential fluorescent materialDetect the application of the adsorbance aspect of dyestuff or luminous agent.
CN201610001152.2A 2016-01-05 2016-01-05 2,5-dibromo-1,4-biphenoxyl cobaltous diacetate complex single crystals and application Pending CN105601506A (en)

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CN105440086A (en) * 2016-01-05 2016-03-30 天津师范大学 Ether acid cobalt complex single crystal and preparation method as well as application thereof
CN106242965A (en) * 2016-07-28 2016-12-21 天津师范大学 2,5 dibromo 1,4 benzene two epoxide zinc diacetate complex monocrystal and application

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CN103421030A (en) * 2013-06-25 2013-12-04 河南大学 Binary aromatic acid cerium complex serving as cadmium ion fluorescent probe, and preparation method of same

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ZHI-MIN LI ET AL.: "Synthesis, crystal structure and thermal analysis of two transition metal coordination compounds based on flexible 2-nitro-benzene-1,4-dioxyacetic acid （NBDOA）", 《JOURNAL OF COORDINATION CHEMISTRY》 *
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105440086A (en) * 2016-01-05 2016-03-30 天津师范大学 Ether acid cobalt complex single crystal and preparation method as well as application thereof
CN106242965A (en) * 2016-07-28 2016-12-21 天津师范大学 2,5 dibromo 1,4 benzene two epoxide zinc diacetate complex monocrystal and application

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Application publication date: 20160525